An Enterprise, such as, a business organization, can store data that may have sensitive content. Such sensitive data can come in the form of private or company information, intellectual property (IP), financial or patient information, credit-card data, and other information depending on the business and the industry. Data loss prevention (DLP) solutions generally detect sensitive data in documents and prevent unauthorized access, saving and/or sharing of the sensitive data. Traditional DLP solutions typically prevent unauthorized access, saving and/or sharing of the sensitive data by monitoring, detecting and blocking sensitive data while in-use (endpoint actions), in-motion (network traffic), and at-rest (data storage). The sensitive data may be stored in digital files. In order to prevent confidential data loss, DLP solutions can create an index of index entries for exact file and partial content matching. The DLP system uses fingerprinting algorithms, such as a one-way hash function, to create fingerprints of the files to be protected. The fingerprints are stored in an index. From a high level perspective, the process of creating a fingerprint includes mapping a larger data item, such as a digital file, to a relatively short set of bytes, known as the fingerprint. For detection, the DLP system creates a fingerprint of a current document and compares the fingerprint against the index for exact file and partial content matching.